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Synlett 2001; 2001(5): 0640-0642
DOI: 10.1055/s-2001-13380
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The Hydrogenation of (4R)-4-[(tert-Butoxycarbonyl)amino]-2-methyl-2-penten-5-olide: A Precursor of trans-4-Methylproline

Marta Nevalainen* , Ari M. P. Koskinen
  • *Laboratory of Organic Chemistry, Helsinki University of Technology, FIN-02015 HUT, Finland; Fax + 358-9-451-2538; E-mail: ari.koskinen@hut.fi
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Publication Date:
31 December 2001 (online)

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(4R)-4[(tert-Butoxycarbonyl)amino]-2-methyl-2-penten-5-olide was synthesized and hydrogenated under various catalyst/solvent systems. The best cis/trans ratio was obtained with Rh/C in diethyl ether (dr = 90 : 10). After one recrystallization, (2S,4R)-4-[(tert-butoxycarbonyl)amino]-2-methylpentan-5-olide was obtained (dr = 95 : 5, ee = 97%), which is a precursor of trans-4-methylproline.

hydrogenation - Garner's aldehyde - alkyl prolines - amino acids - rhodium

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